3, 6, 10-trimethyl-5, 9-undecadien-4-ol and method of making



2,878,295 Patented Mar. 17, 1959 3,6,10-TRllVIETHYL-5,9-UNDECADIEN-4-OL AND 1 METHOD OF MAKING Walter B. Trapp, Midland, Mich., assignor to The Dow Chemical Company, Midland, Micln, a corporation of Delaware No Drawing. Application July 5, 1957 Serial No. 669,937

3 Claims. (Cl. 260-632) This invention pertains to a new compound, 3,6,10- trimethyl-5,9-undecadien-4-ol, and a method of making the same.

The following example illustrates the preparation of this new diene alcohol.

To a 3-molar solution of sec-butyl magnesium bromide in diethyl ether containing 10 gram-moles of the Grignard reagent was added 9 gram-moles of citral as a 65 percent by weight solution in ether. The citral solution was added over a period of approximately three hours while cooling the reaction mixture to maintain the temperature thereof in the range from 25 to 28 C. The resulting reaction mixture was poured with stirring onto a mixture of 10 gram-moles of ammonium chloride and five pounds of crushed ice. The resulting aqueous composition was made acidic to a pH value of approximately by addition thereto of dilute hydrochloric acid. The ethereal layer was separated and was washed with 5 percent by weight sodium carbonate aqueous solution and with water. The resulting ether solution was distilled to a pot temperature of 90 C. at 25 mm. of mercury, absolute pressure. The residue was distilled to obtain a distillate fraction boiling between 98 and 105 C. at 1 mm. of mercury, absolute pressure, and consisting essentially of 3,6,10-trimethyl-S,9-undecadien-4-ol. This new product is a nearly colorless, oily liquid having a specific gravity at 25 C. of approximately 0.86 and a refractive index 12 at 25 C. of approximately 1.470. The product obtained as just described was analyzed with the following results (percent by weight):

Calculated Found or CuHrlDH ingredients in the amounts by weight as shown:

2 3,6,10-trimethyl-5,9-undecadien-4-ol is useful as a specific odor intensifier and modifier for perfume compositions, particularly for floral blends.

The following example illustrates the preparation of one such a perfume composition comprising 3,6,l0-trimethyl-5,9-undecadien-4-ol as an essential ingredient.

A floral base was prepared by mixing the following Parts 3,6,10-trimethyl-S,9-undecadien-4-ol 64 Diethyl phthalate 40 Citronellol 20 Phenylethyl dimethyl carbinol l Benzyl dimethyl carbinol 1 From the resulting fioral base, a rose-type perfume was prepared by mixing the following constituents in the amounts by weight as shown:

Parts Floral base (prepared above) 30 Phenylethyl alcohol 98.8 Citronellol 50 Geraniol ll 4,4-ditolyl ether 10 Geranium Bourbon 0.2 Ethyl alcohol 1800 It will be evident to those skilled in the art that the above-described floral base and perfume are merely illustrative of innumerable such perfume compositions that can be compounded in which 3,6,lO-trimethyl-5,9-undecadien-4-ol is advantageously employed as an essential ingredient together with other ingredients commonly employed in perfume compositions. The resulting perfume compositions are useful in well-known ways in cosmetics, soap, and the like.

That which is claimed is:

1. 3,6,10-trimethyl-S,9-undecadien-4-ol.

2. A perfumery composition of matter comprising as an essential constituent 3,6,10-trimethyl-5,9-undecadien- 4-01.

3. A method which comprises interacting citral with a sec-butyl magnesium Grignard reagent in an ether reaction medium, hydrolyzing' the resulting reaction product with water, and recovering from the hydrolysis reaction product 3,6,10-trimethyl-5,9-undecadien-4-ol.

References Cited in the file of this patent UNITED STATES PATENTS 2,707,196 Woods Apr. 26, 1955 FOREIGN PATENTS 544,388 Germany Feb. 19, 1932 OTHER REFERENCES Austerweil et al.: Comptes Rendus, vol. 151, pages 440-1 (1911); 5 C. A. 2091 (1911).

Fuson: Advanced Organic Chemistry, Wiley, N. Y., 1950; pages 161-3. 

1. 3, 6, 10-TRIMETHYL-5, 9-UNDECADIEN-4-OL. 